EA010026B1 - 4-биарилил-1-фенилазетидин-2-оны - Google Patents

Info

Publication number

EA010026B1

EA010026B1 EA200600950A EA200600950A EA010026B1 EA 010026 B1 EA010026 B1 EA 010026B1 EA 200600950 A EA200600950 A EA 200600950A EA 200600950 A EA200600950 A EA 200600950A EA 010026 B1 EA010026 B1 EA 010026B1

Authority

EA

Eurasian Patent Office

Prior art keywords

fluorophenyl

ethyl acetate

mmol

hydroxypropyl

hexane

Prior art date

2003-11-10

Links

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• Global Dossier
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• 235000000346 sugar Nutrition 0.000 claims abstract description 292
• -1 napfthalene Chemical compound 0.000 claims abstract description 243
• 150000001875 compounds Chemical class 0.000 claims abstract description 211
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
• 150000002367 halogens Chemical class 0.000 claims abstract description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
• 125000003118 aryl group Chemical group 0.000 claims abstract description 24
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
• 239000001257 hydrogen Substances 0.000 claims abstract description 14
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims abstract description 8
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
• 229910052698 phosphorus Inorganic materials 0.000 claims description 11
• 101100027896 Arabidopsis thaliana OCP3 gene Proteins 0.000 claims description 7
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
• 238000011282 treatment Methods 0.000 abstract description 18
• 229910052731 fluorine Inorganic materials 0.000 abstract description 4
• 208000035150 Hypercholesterolemia Diseases 0.000 abstract description 3
• 229910052801 chlorine Inorganic materials 0.000 abstract description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 423
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 243
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 213
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 139
• 239000000203 mixture Substances 0.000 description 121
• 239000011541 reaction mixture Substances 0.000 description 108
• 239000000243 solution Substances 0.000 description 106
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 96
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
• 238000005481 NMR spectroscopy Methods 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 66
• 238000004587 chromatography analysis Methods 0.000 description 62
• 239000000741 silica gel Substances 0.000 description 62
• 229910002027 silica gel Inorganic materials 0.000 description 62
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 62
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 61
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 55
• 239000010802 sludge Substances 0.000 description 53
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 52
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 49
• 239000002253 acid Substances 0.000 description 49
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 48
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
• 229910052938 sodium sulfate Inorganic materials 0.000 description 45
• 235000011152 sodium sulphate Nutrition 0.000 description 45
• 238000000034 method Methods 0.000 description 44
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 44
• 238000000746 purification Methods 0.000 description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 37
• 239000007787 solid Substances 0.000 description 37
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 36
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• 239000012267 brine Substances 0.000 description 31
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
• 229910052757 nitrogen Inorganic materials 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• 125000002252 acyl group Chemical group 0.000 description 25
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 24
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 24
• 235000012000 cholesterol Nutrition 0.000 description 24
• 239000006260 foam Substances 0.000 description 24
• 239000010410 layer Substances 0.000 description 24
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 24
• 210000002966 serum Anatomy 0.000 description 24
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 23
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 125000003282 alkyl amino group Chemical group 0.000 description 20
• 125000004663 dialkyl amino group Chemical group 0.000 description 20
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• 125000005518 carboxamido group Chemical group 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 18
• 229920005862 polyol Polymers 0.000 description 18
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• 238000004007 reversed phase HPLC Methods 0.000 description 17
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 16
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 230000002829 reductive effect Effects 0.000 description 16
• 150000003839 salts Chemical group 0.000 description 16
• 125000004442 acylamino group Chemical group 0.000 description 15
• 239000003814 drug Substances 0.000 description 15
• 239000003112 inhibitor Substances 0.000 description 15
• 150000003077 polyols Chemical class 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 125000005360 alkyl sulfoxide group Chemical group 0.000 description 14
• 230000005764 inhibitory process Effects 0.000 description 14
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 230000002265 prevention Effects 0.000 description 14
• XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 14
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 229930182480 glucuronide Natural products 0.000 description 13
• 150000008134 glucuronides Chemical class 0.000 description 13
• 102100030817 Liver carboxylesterase 1 Human genes 0.000 description 12
• 101710169844 Sesquipedalian-1 Proteins 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• 238000002390 rotary evaporation Methods 0.000 description 12
• 101150072179 ATP1 gene Proteins 0.000 description 11
• 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 11
• 102100021649 Elongator complex protein 6 Human genes 0.000 description 11
• 101100065219 Homo sapiens ELP6 gene Proteins 0.000 description 11
• 101150105046 atpI gene Proteins 0.000 description 11
• 230000001906 cholesterol absorption Effects 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• 206010028980 Neoplasm Diseases 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• 239000004215 Carbon black (E152) Substances 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• 125000005336 allyloxy group Chemical group 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 239000013256 coordination polymer Substances 0.000 description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 241000700159 Rattus Species 0.000 description 8
• 229910052786 argon Inorganic materials 0.000 description 8
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• 125000000524 functional group Chemical group 0.000 description 8
• 125000001072 heteroaryl group Chemical group 0.000 description 8
• 229930195733 hydrocarbon Natural products 0.000 description 8
• 239000004006 olive oil Substances 0.000 description 8
• 235000008390 olive oil Nutrition 0.000 description 8
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
• 230000035484 reaction time Effects 0.000 description 8
• 238000010898 silica gel chromatography Methods 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 210000001519 tissue Anatomy 0.000 description 8
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 7
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 7
• 239000004743 Polypropylene Substances 0.000 description 7
• 229920002472 Starch Polymers 0.000 description 7
• 238000006069 Suzuki reaction reaction Methods 0.000 description 7
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• 125000002947 alkylene group Chemical group 0.000 description 7
• 229910052796 boron Inorganic materials 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000000262 estrogen Substances 0.000 description 7
• 229940011871 estrogen Drugs 0.000 description 7
• 150000002430 hydrocarbons Chemical class 0.000 description 7
• 150000002466 imines Chemical class 0.000 description 7
• 239000004615 ingredient Substances 0.000 description 7
• 150000002632 lipids Chemical class 0.000 description 7
• 238000012544 monitoring process Methods 0.000 description 7
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 7
• 229940049953 phenylacetate Drugs 0.000 description 7
• 229920001155 polypropylene Polymers 0.000 description 7
• 235000019698 starch Nutrition 0.000 description 7
• 229960003080 taurine Drugs 0.000 description 7
• 238000005406 washing Methods 0.000 description 7
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 239000003524 antilipemic agent Substances 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 230000029142 excretion Effects 0.000 description 6
• 229930182470 glycoside Natural products 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 6
• 229940090181 propyl acetate Drugs 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 238000010792 warming Methods 0.000 description 6
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 241000699800 Cricetinae Species 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
• 208000008589 Obesity Diseases 0.000 description 5
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
• 125000003545 alkoxy group Chemical group 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 238000002648 combination therapy Methods 0.000 description 5
• 238000009833 condensation Methods 0.000 description 5
• 230000005494 condensation Effects 0.000 description 5
• RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 150000002338 glycosides Chemical class 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
• 235000020824 obesity Nutrition 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 229910052760 oxygen Inorganic materials 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 238000005086 pumping Methods 0.000 description 5
• 230000002285 radioactive effect Effects 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 150000008163 sugars Chemical class 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• WFWQWTPAPNEOFE-UHFFFAOYSA-N (3-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(O)=C1 WFWQWTPAPNEOFE-UHFFFAOYSA-N 0.000 description 4
• COIQUVGFTILYGA-UHFFFAOYSA-N (4-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(O)C=C1 COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• WNWPMWRKNLBJQO-UHFFFAOYSA-N 2-(3-dimethoxyphosphorylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound COP(=O)(OC)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1 WNWPMWRKNLBJQO-UHFFFAOYSA-N 0.000 description 4
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
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